mu-Methylene-mu-chlorobis(eta5-2,4-cyclopentadien-1-yl)(dimethylaluminum)titanium
Grundinformationen
- CAS
67719-69-1- Standard-SMILES
[CH3-].[CH3][Al][CH3].[Cl-].[Ti+4].c1cc[cH-]c1.c1cc[cH-]c1- InChIKey
JJNHBFYGCSOONU-UHFFFAOYSA-M- Summenformel
- C13H19AlClTi
- Durchschnittliche Molmasse
- 285,59 g/mol
Überblick
Tebbe's reagent is the organometallic compound and titanium and aluminum. It is used in the methylenation of carbonyl compounds. Aluminum is the most abundant metal in the earth's crust and is always found combined with other elements such as oxygen, silicon, and fluorine. (L739, L740, L780)
Namen und Bezeichner
- Bevorzugter Name
- mu-Methylene-mu-chlorobis(eta5-2,4-cyclopentadien-1-yl)(dimethylaluminum)titanium
- Englischer Name
- TEBBE REAGENT
- Summenformel
- C13H4AlClTi
- Molmasse
- 270.47
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
67719-69-1- PubChem CID
- 91617563
- UNII
- V040SDB67S
Eigenschaften
Berechnete Struktureigenschaften
- Polarare Oberfläche (TPSA)
- 0 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 4
- Frei drehbare Bindungen
- 0
- Schwere Atome
- 16
- Formalladung
- 0
- Komplexität
- 14,9
Physikochemische Eigenschaften
- Dichte
- 0.96 g/mL · 0.96 g/mL at 20 °C
- Flammpunkt
- 34 °F · 34 °F
- storage temp.
- Refrigerator
- Aggregatzustand
- Solution
- Farbe
- Dark red to purple
- Wasserlöslichkeit
- Soluble in toluene, benzene, dichloromethane. Insoluble in water.
- Merck
- 9091 · 9091
- InChI
- InChI=1S/2C5.2CH2.C.Al.ClH.Ti/c2*1-2-4-5-3-1;;;;;;/h;;2*1H2;;;1H;/q4*-1;-2;+3;;+4/p-1
- InChIKey
- QEJAQNUJXFLWSP-UHFFFAOYSA-M
- SMILES
- [CH2-][Al+3]1([Cl-][Ti+4]23456789(C%10[C-]2C3=C4C5=%10)(C2[C-]6C7=C8C9=2)[C-2]1)[CH2-]
Sicherheit und Regulatorisches
Gefahrenhinweise
Regulatory Information
Titanium, .mu.-chlorobis(.eta.5-2,4-cyclopentadien-1-yl)(dimethylaluminum)-.mu.-methylene-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Sicherheit und Schutzausrüstung
Toxikologische Informationen
Health Effects
Aluminum targets the nervous system and causes decreased nervous system performance and is associated with altered function of the blood-brain barrier. The accumulation of aluminum in the body may cause bone or brain diseases. High levels of aluminum have been linked to Alzheimer's disease. A small percentage of people are allergic to aluminium and experience contact dermatitis, digestive disorders, vomiting or other symptoms upon contact or ingestion of products containing aluminium. (L739, L740)
Toxicity Summary
The main target organs of aluminum are the central nervous system and bone. Aluminum binds with dietary phosphorus and impairs gastrointestinal absorption of phosphorus. The decreased phosphate body burden results in osteomalacia (softening of the bones due to defective bone mineralization) and rickets. Aluminum's neurotoxicity is believed to involve several mechanisms. Changes in cytoskeletal protein functions as a results of altered phosphorylation, proteolysis, transport, and synthesis are believed to be one cause. Aluminum may induce neurobehavioral effects by affecting permeability of the blood-brain barrier, cholinergic activity, signal transduction pathways, lipid peroxidation, and impair neuronal glutamate nitric oxide-cyclic GMP pathway, as well as interfere with metabolism of essential trace elements because of similar coordination chemistries and consequent competitive interactions. It has been suggested that aluminum's interaction with estrogen receptors increases the expression of estrogen-related genes and thereby contributes to the progression of breast cancer (A235), but studies have not been able to establish a clear link between aluminum and increased risk of breast cancer (A15468). Certain aluminum salts induce immune responses by activating inflammasomes. (L739, A235, A236)
Signs and Symptoms
Inhalating aluminum dust causes coughing and abnormal chest X-rays. A small percentage of people are allergic to aluminium and experience contact dermatitis, digestive disorders, vomiting or other symptoms upon contact or ingestion of products containing aluminium. (L739, L740)
Carcinogen Classification
Not listed by IARC. IARC classified aluminum production as carcinogenic to humans (Group 1), but did not implicate aluminum itself as a human carcinogen. (L135) A link between use of aluminum-containing antiperspirants and increased risk of breast cancer has been proposed (A235), but studies have not been able to establish a clear link (A15468).
Sicherheitsdaten
- F
- 1-10
- wgk
- 2
- ridadr
- UN 2924 3/PG 2
- hs_code
- 29310099
- risk_code
- 11-34-48/20-63-65-67
- hazard_code
- F,C
- safety_code
- 26-36/37/39-45-62-16
- hazard_class
- 4.3
- packing_group
- II
- Speicherklasse
- 3 - Flammable liquids
- Hazard Classifications
- Aquatic Chronic 3Asp. Tox. 1Eye Dam. 1Flam. Liq. 2Repr. 2Skin Corr. 1BSTOT RE 2STOT SE 3
Chemie und Industrie
Pharmakologische Informationen
Metabolism/Metabolites
Aluminum is poorly absorbed following either oral or inhalation exposure and is essentially not absorbed dermally. The bioavailability of aluminum is strongly influenced by the aluminum compound and the presence of dietary constituents which can complex with aluminum and enhance or inhibit its absorption. Aluminum binds to various ligands in the blood and distributes to every organ, with highest concentrations found in bone and lung tissues. In living organisms, aluminum is believed to exist in four different forms: as free ions, as low-molecular-weight complexes, as physically bound macromolecular complexes, and as covalently bound macromolecular complexes. Absorbed aluminum is excreted principally in the urine and, to a lesser extent, in the bile, while unabsorbed aluminum is excreted in the faeces. (L739)
Verwendung und Herstellung
Anwendungen
Verwendenμ-Chloro-μ-methylenebis(cyclopentadienyl)titaniumdimethylaluminum is used in organic synthesis for carbonyl methylenation, A versatile methylenation reagent for the conversion of ketones and aldehydes to olefins, it offers facile reaction with hindered ketones and allows the conversion of esters to vinyl ethers. Tebbe reagent can be used to olefinate aldehydes, to methylenate a chiral polyhydroxyketone with high diasteroselctivity.
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